HCID 57917486, compound → 6-[6-(1-Methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-7-trifluoromethyl-quinoline

HRID 69208Notes

Reaction equation

HRID 69208 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8](Cl)[CH:9]=[CH:10]C2=NC=1.Cl[C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([CH:22]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][C:33]=3[C:34]([F:37])([F:36])[F:35])[N:30]=[CH:29][CH:28]=[CH:27]4)O)=[CH:20][N:21]=2)[N:18]=1.C([Mg]Br)C.FC(F)(F)C1C=C2C(C=CC=N2)=CC=1C=O>C1COCC1>[CH3:2][N:6]1[CH:10]=[C:9]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([CH2:22][C:24]4[CH:25]=[C:26]5[C:31](=[CH:32][C:33]=4[C:34]([F:37])([F:35])[F:36])[N:30]=[CH:29][CH:28]=[CH:27]5)=[CH:20][N:21]=3)[N:18]=2)[CH:8]=[N:7]1

Participants

5

Reactant 3

HCID 57917486HCID 57917486, compound2×HCID 87680477(rac)-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(7-trifluoromethyl-quinolin-6-yl)-methanol 3-Bromo-6-chloro-imidazo[1,2-b]pyridazineHCID 178418443HCID 178418443, compound

Product 1

HCID 579172686-[6-(1-Methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-7-trifluoromethyl-quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(rac)-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(7-trifluoromethyl-quinolin-6-yl)-methanol 3-Bromo-6-chloro-imidazo[1,2-b]pyridazine (500 mg, 2.15 mmol) was dissolved THF (50 mL) and under nitrogen conditions, ethylmagnesium bromide solution (3 M, 0.860 mL) was added. The RM was stirred at rt for 30 min then a solution of 7-trifluoromethyl-quinoline-6-carbaldehyde (Intermediate G, 723 mg, 2.15 mmol) in THF was added. It was stirred at rt for 1 h. The solvent was removed and the residue was taken up with EtOAc and washed with water and brine. It was dried over Na2SO4 and the solvent was evaporated in vacuo. The residue was triturated with Et2O and the precipitate was filtered off. The title compound was obtained as a grey solid (tR 1.48 min (conditions 12), MH+=379).

Workup

  1. stirringIt was stirred at rt for 1 h
  2. customThe solvent was removed
  3. washwashed with water and brine
  4. dry with materialIt was dried over Na2SO4
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was triturated with Et2O
  7. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-01d69feaba7a4bfb9fe8bd98604785f9
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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